Hmm.. while his actions come from a good place, the way he put it shows his lack of understanding and empathy. My problem with him is that he acts as if he knows everything when he hasn't even lived that long. Rather, he really shouldn't assume he knows things better than others, and should be more transparent with his words. It's worthless if you simply imply things instead of being straightforward. Sometimes, the whole mysterious and wise persona should be set aside for saying things directly. The main reason he even hurt the girl is because he wasn't clear enough. If he said "I will only take your V if you fully commit yourself to me and not for a transaction" things might have gone differently, so he is not as gentlemanly and smart as he thinks he is.
For me he is quite a naive protagonist that you can find anywhere, at least those in 15-30 years old from Earth who got reincarnated in fantasy world will change their perspective, but here he is like a 5 years old, even though he already the strongest in his previous world he still naive in feelings, i don't know if he really understand women's feelings even though he save many women in his previous life and see their life experiences when he save them, he is like a stubborn person and don't want to change his perspective that is how I see it.
I think a lot of readers struggle with the fact he did the one thing every man/boy over the age of 10 on the planet knows is the worse thing you can do when there is any intimacy bring up another woman/compare a woman to her sister. He could have said "sorry I am not ready to go this far with you. Your virginity is something I someone who has already lived for centuries am not willing to take at this time." and I think most would have sided with him and felt he did the right thing. Or even just "Sorry if you are going to give you virginity, you need to do be not under the effect of a special physique like mine, and especially not as a business transaction."